US4173638A - N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof - Google Patents

N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof Download PDF

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US4173638A
US4173638A US05/844,174 US84417477A US4173638A US 4173638 A US4173638 A US 4173638A US 84417477 A US84417477 A US 84417477A US 4173638 A US4173638 A US 4173638A
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phenyl
urea
oxy
chlorobenzoyl
dichloropyridyl
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Ryuzo Nishiyama
Kanichi Fujikawa
Rikuo Nasu
Tadaaki Toki
Toshihiko Yamamoto
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Ishihara Sangyo Kaisha Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6

Definitions

  • the present invention relates to novel N-benzoyl N'-pyridyloxy phenyl ureas and the process for producing the same and the insecticidal composition containing the same.
  • N-benzoyl N'-phenyl ureas disclosed in U.S. Pat. No. 3,748,356 have such insecticidal properties.
  • N-benzoyl N'-pyridyloxyphenyl ureas according to the present invention have a substantially better action than the above described known compounds.
  • novel compounds of the present invention are N-benzoyl N'-pyridyloxy phenyl ureas having the formula ##STR2## wherein X 1 represents a halogen atom; X 2 represents hydrogen or halogen atom; X 3 and X 4 respectively represent hydrogen or chlorine atom; X 5 represents hydrogen or halogen atom; and X 6 represents a halogen atom or nitro or trifluoromethyl group.
  • Suitable compounds having the formula (I) include:
  • N-benzoyl N'-pyridyloxy phenyl ureas having the formula (I) are produced by reacting a compound having the formula ##STR3## wherein X 1 represents a halogen atom; X 2 represents hydrogen or halogen atom; R 1 represents amino or isocyanate group with a compound having the formula ##STR4## wherein X 3 and X 4 are the same and different and respectively represent hydrogen or chlorine atom; X 5 represents hydrogen or halogen atom; X 6 represents halogen atom or nitro or trifluoromethyl group; and R 2 represents an amino or isocyanate group and R 2 is amino group in the case that R 1 is isocyanate group, R 2 is isocyanate group in the case that R 1 is amino group.
  • the compounds having the formula (I) can be produced by the following processes (1) and (2).
  • the reaction is preferably carried out in the presence of a solvent.
  • Suitable solvents include benzene, toluene, xylene, pyridine etc.
  • the reaction temperature is usually in a range of 20° to 120° C. and the reaction time is usually in a range of 0.5 to 24 hours.
  • the reaction is preferably carried out at the temperature from 50° C. to a refluxing temperature for 1 to 5 hours.
  • a solution prepared by dissolving 2.9 g of 3-chloro-4-(3,5-dichloro-pyridyl-2-oxy) aniline in 50 ml of toluene was heated at 80° C.
  • a solution prepared by dissolving 1.8 g of 2-chlorobenzoyl isocyanate in 20 ml of toluene was added dropwise to the former solution under stirring it and the reaction was carried out for 1 hour.
  • Example 2 In accordance with the process of Example 1, except using 2.5 g of 4-(3,5-dichloropyridyl-2-oxy) aniline instead of 3-chloro-4-(3,5-dichloropyridyl-2-oxy) aniline and using 2.4 g of 2,6-dichlorobenzoyl isocyanate instead of 2-chlorobenzoyl isocyanate and reacting at 30° C. for 8 hours instead of 80° C. for 1 hour, the process was repeated to obtain 3.8 g of N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea (m.p. 228° to 230° C.).
  • the compounds of the present invention impart excellent selective insecticidal effect as clearly understood from the following experiments.
  • the compounds of the present invention impart the delayed effect that the compounds effect to molting (ecdysis) and metamorphosis of specific insects which orally take the compound with feeds or water whereby the death of the specific insects is caused.
  • the compounds of the present invention impart remarkable insecticidal effect to larvae of Lepidoptera, Coleoptera, Hymenoptera and Diptera, for example, larvae of the following insects:
  • the compounds of the present invention do not substantially impart insecticidal effect to adults and are ineffective to natural enemies as predatory insects and impart low toxicity to animals.
  • compositions such as dust, wettable powder, emulsifiable concentrate, invert emulsion, oil solution, aerosol preparation, etc. with adjuvants as the cases of agricultural compositions.
  • the compositions can be applied with or without diluting them in suitable concentrations.
  • Suitable adjuvants include powdery carriers such as talc, kaolin, bentonite, diatomaceous earth, silicon dioxide, clay and starch; liquid diluents such as water, xylene, toluene, dimethylsulfoxide, dimethyl formamide, acetonitrile, and alcohol; emulsifiers dispersing agents spreaders etc.
  • the concentration of the active ingredient in the selective insecticidal composition is usually 5 to 80 wt.% in the case of the oily concentrate; and 0.5 to 30 wt.% in the case of dust; 5 to 60 wt.% in the case of wettable powder.
  • the selective insecticides of the present invention are effective for inhibiting various injurious insects and they are usually applied at a concentration of the active ingredients of 5 to 10,000 ppm preferably 20 to 2,000 ppm.
  • the active ingredients were respectively dispersed in water to prepare dispersions having specified concentrations. Leaves of cabbage were dipped into the dispersions for about 10 seconds and taken out and dried under passing air.
  • Young branches of persimmon tree cut in a length of 15 cm from the top were respectively dipped into the aqueous dispersions of N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea at various concentrations for 10 seconds, and they were dried and put into wide mouth bottles and larvae of gypsy moth in 2nd or 3rd instar were fed into them.
  • the bottles were covered with gauze and kept in a constant temperature at 28° C. with lightening. After 7 days and 15 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates and the abnormal rates were calculated. The results are shown in Table 4.
  • N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy)phenyl]urea was used to prepare the aqueous dispersions at specified concentrations. The effects of the dispersions to various insects were tested. The mortality rates after 10 days from the treatments were obtained in accordance with the process of Experiment 1.
  • the components were uniformly blended to dissolve the ingredient to prepare an emulsifiable concentrate.
  • the mixture was pulverized to uniformly mix them to prepare dust.
  • the components were pulverized to uniformly mix them to prepare a wettable powder.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

N-benzoyl N'-pyridyloxy phenyl urea having the formula ##STR1## wherein X1 represents a halogen atom; X2 represents hydrogen or halogen atom; X3 and X4 respectively represent hydrogen or chlorine atom; X5 represents hydrogen or halogen atom; and X6 represents a halogen atom or nitro or trifluoromethyl group are novel compounds.
The compositions containing the compound as the active ingredient are effective as the insecticide for extinction of injurious insects with high safety in agricultural, forestry and hygienic applications.

Description

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel N-benzoyl N'-pyridyloxy phenyl ureas and the process for producing the same and the insecticidal composition containing the same.
2. Description of the Prior Arts
Almost of the conventional insecticides impart neurotoxicity and contact toxicity to all kinds of insects.
And, it has been required to find selective insecticidal compounds without toxicity to useful insects, N-benzoyl N'-phenyl ureas disclosed in U.S. Pat. No. 3,748,356 have such insecticidal properties.
The N-benzoyl N'-pyridyloxyphenyl ureas according to the present invention have a substantially better action than the above described known compounds.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide novel N-benzoyl N'-pyridyloxy phenyl ureas.
It is another object of the present invention to provide a process for producing N-benzoyl N'-pyridyloxy phenyl ureas.
It is the other objects of the present invention to provide selective insecticidal compositions which are remarkably effective to certain injurious insects without affecting useful insects in remarkably low toxicity to animals.
The novel compounds of the present invention are N-benzoyl N'-pyridyloxy phenyl ureas having the formula ##STR2## wherein X1 represents a halogen atom; X2 represents hydrogen or halogen atom; X3 and X4 respectively represent hydrogen or chlorine atom; X5 represents hydrogen or halogen atom; and X6 represents a halogen atom or nitro or trifluoromethyl group.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Suitable compounds having the formula (I) include:
N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-bromopyridyl-2-oxy) phenyl]urea m.p. 196° to 199° C.
N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-nitropyridyl-2-oxy) phenyl]urea m.p. 209° to 212° C.
N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy) phenyl]urea m.p. 185° to 188° C.
N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dibromopyridyl-2-oxy) phenyl]urea m.p. 223° to 224° C.
N-(2-chlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 216° to 218° C.
N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 225° to 228° C.
N-(2-chlorobenzoyl)N'-[3,5-dichloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 221° to 223° C.
N-(2-chlorobenzoyl)N'-[4-(5-bromopyridyl-2-oxy) phenyl]urea m.p. 179° to 180° C.
N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-chloropyridyl-2-oxy) phenyl]urea m.p. 198° to 200° C.
N-(2-chlorobenzoyl)N'-[3,5-dichloro-4-(5-chloropyridyl-2-oxy) phenyl]urea m.p. 147° to 148° C.
N-(2-chlorobenzoyl)N'-[4-(5-trifluoromethylpyridyl-2-oxy) phenyl]urea
N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-trifluoromethylpyridyl-2-oxy) phenyl]urea
N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 228° to 230° C.
N-(2,6-dichlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 214° to 216° C.
N-(2,6-dichlorobenzoyl)N'-[3,5-dichloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 273° to 275° C.
N-(2,6-difluorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 184° to 185° C.
N-(2,6-difluorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea m.p. 230° to 231° C.
N-(2,6-difluorobenzoyl)N'-[3-chloro-4-(5-chloropyridyl-2-oxy) phenyl]urea m.p. 210° to 212° C.
The N-benzoyl N'-pyridyloxy phenyl ureas having the formula (I) are produced by reacting a compound having the formula ##STR3## wherein X1 represents a halogen atom; X2 represents hydrogen or halogen atom; R1 represents amino or isocyanate group with a compound having the formula ##STR4## wherein X3 and X4 are the same and different and respectively represent hydrogen or chlorine atom; X5 represents hydrogen or halogen atom; X6 represents halogen atom or nitro or trifluoromethyl group; and R2 represents an amino or isocyanate group and R2 is amino group in the case that R1 is isocyanate group, R2 is isocyanate group in the case that R1 is amino group.
More particularly, the compounds having the formula (I) can be produced by the following processes (1) and (2).
(1) The reaction of benzoyl isocyanate having the formula ##STR5## with pyridyloxy aniline having the formula ##STR6## (wherein X1, X2, X3, X4, X5 and X6 are defined above)
(2) The reaction of benzamide having the formula ##STR7## with pyridyloxy phenyl isocyanate having the formula ##STR8## (wherein X1, X2, X3, X4, X5, and X6 are defined above).
The reaction is preferably carried out in the presence of a solvent. Suitable solvents include benzene, toluene, xylene, pyridine etc.
The reaction temperature is usually in a range of 20° to 120° C. and the reaction time is usually in a range of 0.5 to 24 hours. The reaction is preferably carried out at the temperature from 50° C. to a refluxing temperature for 1 to 5 hours.
Certain examples of preparations of the compounds of the present invention will be described.
EXAMPLE 1 Preparation of N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy) phenyl]urea
A solution prepared by dissolving 2.9 g of 3-chloro-4-(3,5-dichloro-pyridyl-2-oxy) aniline in 50 ml of toluene was heated at 80° C. A solution prepared by dissolving 1.8 g of 2-chlorobenzoyl isocyanate in 20 ml of toluene was added dropwise to the former solution under stirring it and the reaction was carried out for 1 hour. After the reaction, the reaction mixture was cooled and the precipitate was filtered and washed with toluene and then with petroleum ether and dried to obtain 3.2 g of N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea (m.p. 225° to 228° C.).
EXAMPLE 2 Preparation of N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea
In accordance with the process of Example 1, except using 2.5 g of 4-(3,5-dichloropyridyl-2-oxy) aniline instead of 3-chloro-4-(3,5-dichloropyridyl-2-oxy) aniline and using 2.4 g of 2,6-dichlorobenzoyl isocyanate instead of 2-chlorobenzoyl isocyanate and reacting at 30° C. for 8 hours instead of 80° C. for 1 hour, the process was repeated to obtain 3.8 g of N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy) phenyl]urea (m.p. 228° to 230° C.).
The compounds of the present invention impart excellent selective insecticidal effect as clearly understood from the following experiments.
Most of the conventional insecticides impart quick effect and neurotoxicity and contact toxicity. However, the compounds of the present invention impart the delayed effect that the compounds effect to molting (ecdysis) and metamorphosis of specific insects which orally take the compound with feeds or water whereby the death of the specific insects is caused.
The compounds of the present invention impart remarkable insecticidal effect to larvae of Lepidoptera, Coleoptera, Hymenoptera and Diptera, for example, larvae of the following insects:
diamondback moth (Plutella xylostella), common white (Pieris rapae crucivora), cabbage armyworm (Mamesta brassicae), cabbage looper (Plusia nigrisigma), tobacco cutworm (Prodenia litura), smoller citrus dog (Papilio xuthus), small blackfish cochlid (Seopelodes contracta), fall webworm (Hyphantria cunea), gypsy moth (Lymantria dispar), rice stem borer (Chilo suppressalis), bollworm (Heliothis zea), tobacco budworm (Heliothis virescens), bollweevil (Anthonomus grandis), confused flour beetle (Tribolium confusum), colorado potato beetle (Leptinotarsa decemlineata), sawfly (Neurotoma irdescens), Culex mosquito (Culex pipiens pallens).
The compounds of the present invention do not substantially impart insecticidal effect to adults and are ineffective to natural enemies as predatory insects and impart low toxicity to animals.
When the compounds are used as active ingredients of the insecticidal composition, it is possible to prepare various forms of the compositions such as dust, wettable powder, emulsifiable concentrate, invert emulsion, oil solution, aerosol preparation, etc. with adjuvants as the cases of agricultural compositions. The compositions can be applied with or without diluting them in suitable concentrations.
Suitable adjuvants include powdery carriers such as talc, kaolin, bentonite, diatomaceous earth, silicon dioxide, clay and starch; liquid diluents such as water, xylene, toluene, dimethylsulfoxide, dimethyl formamide, acetonitrile, and alcohol; emulsifiers dispersing agents spreaders etc.
The concentration of the active ingredient in the selective insecticidal composition is usually 5 to 80 wt.% in the case of the oily concentrate; and 0.5 to 30 wt.% in the case of dust; 5 to 60 wt.% in the case of wettable powder.
It is also possible to combine with the other agricultural ingredients such as the other insecticides, miticides, plant growth regulators. Sometimes synergetic effects are found.
The selective insecticides of the present invention are effective for inhibiting various injurious insects and they are usually applied at a concentration of the active ingredients of 5 to 10,000 ppm preferably 20 to 2,000 ppm.
EXPERIMENT 1
The active ingredients were respectively dispersed in water to prepare dispersions having specified concentrations. Leaves of cabbage were dipped into the dispersions for about 10 seconds and taken out and dried under passing air.
A piece of moistened filter paper was put on each Petri dish (diameter 9 cm) and the dried leaves of cabbage were put on the filter paper and larvae of diamondback moth in 2nd or 3rd instar were fed on them and the Petri dishes were covered and kept in constant temperature at 28° C. with lightening. After 8 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates were calculated by the following equation: ##EQU1##
              Table 1                                                     
______________________________________                                    
                        Mortality                                         
                        Rate                                              
                        (%)                                               
                        (concen-                                          
                         tration)                                         
                              200    100                                  
No.  Active ingredient        ppm    ppm                                  
______________________________________                                    
1    N-(2-chlorobenzoyl)N'-[3-chloro-4(5-bromo-                           
     pyridyl-2-oxy)phenyl]urea                                            
                              100    100                                  
2    N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-nitro-                          
     pyridyl-2-oxy)phenyl]urea                                            
                              100    100                                  
3    N-(2-chlorobenzoyl)N'-[4-(3,5-dibromo-                               
     pyridyl-2-oxy)phenyl]urea                                            
                              100    100                                  
4    N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-                              
     dibromopyridyl-2-oxy)phenyl]urea                                     
                              100    100                                  
5    N-(2-chlorobenzoyl)N'-[4-(3,5-dichloro-                              
     pyridyl-2-oxy)phenyl]urea                                            
                              100    100                                  
6    N-(2-chlorobenzoyl)N'-[3-chloro-4-                                   
     (3,5-dichloropyridyl-2-oxy)phenyl]urea                               
                              100    100                                  
7    N-(2,6-dichlorobenzoyl)N-[4-(3,5-                                    
     dichloropyridyl-2-oxy)phenyl]urea                                    
                              100    100                                  
8    N-(2,6-dichlorobenzoyl)N'-[3-chloro-                                 
     4-(3,5-dichloropyridyl-2-oxy)phenyl]urea                             
                              100    100                                  
9    N-(2-chlorobenzoyl)N'-[3,5-dichloro-4-                               
     (3,5-dichloropyridyl-2-oxy)phenyl]urea                               
                              100     80                                  
10   N-(2,6-dichlorobenzoyl)N'-[3,5-dichloro-                             
     4-(3,5-dichloropyridyl-2-oxy)phenyl]urea                             
                               80     60                                  
11   N-(2,6-difluorobenzoyl)N'-[4-(3,5-                                   
     dichloropyridyl-2-oxy)phenyl]urea                                    
12   100                                                                  
12   N-(2,6-difluorobenzoyl)N'-[3-chloro-4-                               
     (3,5-dichloropyridyl-2-oxy)phenyl]urea                               
                              100    100                                  
13   N-(2-chlorobenzoyl)N'-[4-(5-bromo-                                   
     pyridyl-2-oxy)phenyl]urea                                            
                              100    100                                  
14   N-(2-chlorobenzoyl)N'-[3-chloro-4-                                   
     (5-chloropyridyl-2-oxy)phenyl]urea                                   
                              100    100                                  
15   N-(2-chlorobenzoyl)N'-[3,5-dichloro-4-                               
     (5-chloropyridyl-2-oxy)phenyl]urea                                   
                              100     60                                  
16   N-(2-chlorobenzoyl)N'-[4-(5-trifluoro-                               
     methylpyridyl-2-oxy)phenyl]urea                                      
                              100     80                                  
17   N-(2,6-difluorobenzoyl)N'-[3-chloro-4-                               
     (5-chloropyridyl-2-oxy)phenyl]urea                                   
                              100    100                                  
______________________________________
EXPERIMENT 2
On radish young seedlings grown in unglazed pots, adults of diamondback moth were fed and kept for 24 hours to blow ova. One day later, aqueous dispersions of the active ingredients (500 ppm) were respectively sprayed on the young seedlings to fall drops of the dispersion and dried and kept in glass greenhouse. After 10 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates were calculated by the equation ##EQU2##
The results are shown in Table 2.
              Table 2                                                     
______________________________________                                    
                            Mortality rate                                
NO.  Active ingredient      (%)                                           
______________________________________                                    
1    N-(2-chlorobenzoyl)N'-[3-chloro-4-                                   
     (5-nitropyridyl-2-oxy)phenyl]urea                                    
                             80                                           
2    N-(2-chlorobenzoyl)N'-[3-chloro-4-                                   
     (3,5-dibromopyridyl-2-oxy)phenyl]urea                                
                            100                                           
3    N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-                              
     dichloropyridyl-2-oxy)phenyl]urea                                    
                            100                                           
______________________________________
EXPERIMENT 3
About 20 cc of germinated rice seeds were put into cups (diameter: 9 cm, height: 3 cm) to grow them. When they grew to seedlings having a height of 1 to 2 cm, the aqueous dispersions at specified concentrations were respectively sprayed at a ratio of 2 cc per 1 cup and dried, and larvae of rice stem borer (just hatched) were fed and the cups were covered. After 10 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates were calculated by the equation of Experiment 1. The results are shown in Table 3.
              Table 3                                                     
______________________________________                                    
                     Mortality rate (%)                                   
                     (concentration)                                      
No.  Active ingredient     200 ppm  100 ppm                               
______________________________________                                    
1    N-(2-chlorobenzoyl)N'-[3-chloro-4-                                   
      (5-bromopyridyl-2-oxy) phenyl] urea                                 
                           100      100                                   
2    N-(2-chlorobenzoyl)N'-[3-chloro-4-                                   
      (5-nitropyridyl-2-oxy) phenyl] urea                                 
                           100      100                                   
3    N-(2-chlorobenzoyl)N'-[3-chloro-4-                                   
      (3,5-dibromopyridyl)-2-oxy) phenyl]                                 
      urea                 100      100                                   
4    N-(2-chlorobenzoyl)N'-[3-chloro-4-                                   
      (3,5-dichloropyridyl-2-oxy) phenyl]                                 
      urea                 100      100                                   
______________________________________
EXPERIMENT 4
Young branches of persimmon tree cut in a length of 15 cm from the top, were respectively dipped into the aqueous dispersions of N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea at various concentrations for 10 seconds, and they were dried and put into wide mouth bottles and larvae of gypsy moth in 2nd or 3rd instar were fed into them. The bottles were covered with gauze and kept in a constant temperature at 28° C. with lightening. After 7 days and 15 days from the treatment with the dispersion, the dead larvae were measured and the mortality rates and the abnormal rates were calculated. The results are shown in Table 4.
              Table 4                                                     
______________________________________                                    
            Mortality rate (%)                                            
            (concentration)                                               
Observation   400 ppm   200 ppm   100 ppm                                 
______________________________________                                    
After 7 days  100       90 (10)*  40 (30)*                                
After 15 days 100       100       90 (10)*                                
______________________________________                                    
  *abnormal rate
EXPERIMENT 5
N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy)phenyl]urea was used to prepare the aqueous dispersions at specified concentrations. The effects of the dispersions to various insects were tested. The mortality rates after 10 days from the treatments were obtained in accordance with the process of Experiment 1.
The results are shown in Table 5.
              Table 5                                                     
______________________________________                                    
                           Concent-                                       
                           ration   Mortality                             
Insects        Treatment   (ppm)    rate                                  
______________________________________                                    
cabbage armyworm:                                                         
               cabbage leaf                                               
2nd instar larvae                                                         
               dipping      50      100                                   
(Lepidoptera)                                                             
confused flour beetle:                                                    
               wheat flour                                                
2nd larval instar larvae                                                  
               blending    200      100                                   
(Coleoptera)                                                              
1 sp. of sawfly                                                           
               cherry branch                                              
3rd instar larvae                                                         
               spraying    250      100                                   
(Hymenoptera)                                                             
______________________________________
EXPERIMENT 6
200 ml of the aqueous dispersions at specified concentrations were respectively placed in glass containers with a capacity of 450 cc. 20 larvae of third instar of the mosquito (Culex pipiens pallens) were placed in each container and the containers were hold at 26°-28° C. with lightening. The mortality rates after 10 days from the treatments were obtained in accordance with the process of Experiment 1.
The results are shown in Table 6.
              Table 6                                                     
______________________________________                                    
                    Mortality rate (%)                                    
No.  Active ingredient    0.1 ppm  0.01 ppm                               
______________________________________                                    
1    N-(2-chlorobenzoyl)N'-[4-(3,5-                                       
     dibromopyridyl-2-oxy)phenyl] urea                                    
                          100      100                                    
2    N-(2,6-difluorobenzoyl)N'-[4-(3,5-                                   
     dichloropyridy-2-oxy)phenyl] urea                                    
                          100      100                                    
3    N-(2-chlorobenzoyl)N'-[4-(5-bromo-                                   
     pyridyl)-2-oxy)phenyl] urea                                          
                          100      100                                    
______________________________________
COMPOSITION 1 
______________________________________                                    
(a)  N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-              
     2-oxy)phenyl]urea      20 wt. parts                                  
(b)  Dimethyl sulfoxide     70 wt. parts                                  
(c)  Polyoxyethylenealkylphenyl ether                                     
                            10 wt. parts                                  
______________________________________
The components were uniformly blended to dissolve the ingredient to prepare an emulsifiable concentrate.
COMPOSITION 2 
______________________________________                                    
(a) N-(2-chlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]           
    urea                   5 wt. parts                                    
(b) Talc                   92 wt. parts                                   
(c) Sodium naphthalene sulfonate                                          
    formaldehyde condensate                                               
                           3 wt. parts                                    
______________________________________
The mixture was pulverized to uniformly mix them to prepare dust.
COMPOSITION 3 
______________________________________                                    
(a)   N-(2,6-dichlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy             
      phenyl]urea          50 wt. parts                                   
(b)   Jeeklite (fine divided clay)                                        
                           45 wt. parts                                   
(d)   Sodium ligninsulfonate                                              
                            5 wt. parts                                   
______________________________________
The components were pulverized to uniformly mix them to prepare a wettable powder.

Claims (17)

What is claimed is:
1. N-benzoyl N'-pyridyloxy phenyl urea having the formula ##STR9## wherein X1 represents a halogen atom; X2 represents hydrogen or halogen atom; X3 and X4 respectively represent hydrogen or chlorine atom; X5 represents hydrogen or halogen atom; X6 represents a halogen atom or nitro or trifluoromethyl group.
2. N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 which has the formula ##STR10## wherein X7 represents hydrogen or chlorine atom and X8 represents hydrogen or halogen atom; X9 represents a halogen atom.
3. N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy)phenyl]urea.
4. N-(2-chlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
5. N-(2-chlorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
6. N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-chloropyridyl-2-oxy)phenyl]urea.
7. N-benzoyl N'-pyridyloxy phenyl urea according to claim 1 which has the formula: ##STR11## wherein X7, X8 and X9 are defined in claim 2.
8. N-(2,6-difluorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
9. N-(2,6-difluorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
10. An insecticidal composition which comprises insecticidally effective amount N-benzoyl N'-pyridyloxy phenyl urea having the formula (I) according to claim 1 in admixture with a suitable carrier or adjuvant therefor.
11. An insecticidal composition according to claim 10 which comprises 0.5 to 80 wt. parts of N-benzoyl N'-pyridyloxy phenyl urea having the formula (I) and 20 to 99.5 wt. parts of an agricultural adjuvant.
12. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2-chlorobenzoyl)N'-[4-(3,5-dibromopyridyl-2-oxy)phenyl]urea.
13. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2-chlorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
14. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2-[chlorobenzoyl)N'-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
15. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2-chlorobenzoyl)N'-[3-chloro-4-(5-chloropyridyl-2-oxy)phenyl]urea.
16. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2,6-difluorobenzoyl)N'-[4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
17. An insecticidal composition according to claim 10 wherein the active ingredient is N-(2,6-difluorobenzoyl)N'-[3-chloro-4-(3,5-dichloropyridyl-2-oxy)phenyl]urea.
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US4223033A (en) * 1979-08-24 1980-09-16 Zoecon Corporation Substituted pyridine methyl esters of naphthyl acids
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US4310530A (en) * 1979-09-07 1982-01-12 Ishihara Sangyo Kaisha Ltd. N-benzoyl N-pyridyloxy phenyl urea
US4321388A (en) * 1979-09-11 1982-03-23 Ishihara Sangyo Kaisha Ltd. N-benzoyl N'-pyridyloxy phenyl urea
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US4431667A (en) * 1981-12-04 1984-02-14 The Upjohn Company Imino ethers useful for controlling insect and arachnoid pests
US4540578A (en) * 1982-12-30 1985-09-10 Union Carbide Corporation Pesticidal phenoxypyridyl benzoyl ureas
US4577028A (en) * 1981-10-20 1986-03-18 Ciba-Geigy Corporation 5-Haloalkyl-pyridines
US4602109A (en) * 1982-12-30 1986-07-22 Union Carbide Corporation Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation
US4659724A (en) * 1982-12-30 1987-04-21 Union Carbide Corporation Certain 1-[4-(5-cyano-2-pyridyloxy)phenyl-benzoyl ureas having pesticidal properties
US4677127A (en) * 1981-11-10 1987-06-30 Ciba-Geigy Corporation Certain N-3-(3-chloro-5-trifluoromethyl-pyridyl-2-oxy)-4-phenyl-N'-2,6-difluorobenzoyl ureas, pesticidal compositions and methods of use
US4861799A (en) * 1986-10-03 1989-08-29 Ishihara Sangyo Kaisha Ltd. Benzoylurea compounds and pesticides containing them
US4973589A (en) * 1986-08-06 1990-11-27 Ciba-Geigy Corporation Method of preventing the reinfestation of dogs and cats by fleas
US5036072A (en) * 1989-01-24 1991-07-30 Ishihara Sangyo Kaisha Ltd. Antiviral agent
US5098907A (en) * 1989-01-24 1992-03-24 Ishihara Sangyo Kaisha Ltd. Powdery pharmaceutical composition containing benzoyl urea, a dispersant and silicic acid
US5728719A (en) * 1991-12-23 1998-03-17 Virbac, Inc. Systemic control of parasites
US6344476B1 (en) 1997-05-23 2002-02-05 Bayer Corporation Inhibition of p38 kinase activity by aryl ureas
US20040023961A1 (en) * 2002-02-11 2004-02-05 Bayer Corporation Aryl ureas with raf kinase and angiogenisis inhibiting activity
US20070020704A1 (en) * 2003-05-20 2007-01-25 Scott Wilhelm Diaryl ureas with kinase inhibiting activity
US7235576B1 (en) 2001-01-12 2007-06-26 Bayer Pharmaceuticals Corporation Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US20080009527A1 (en) * 1997-12-22 2008-01-10 Jacques Dumas Inhibition of raf kinase using aryl and heteroaryl substituted heterocyclic ureas
US7351834B1 (en) 1999-01-13 2008-04-01 Bayer Pharmaceuticals Corporation ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7371763B2 (en) 2001-04-20 2008-05-13 Bayer Pharmaceuticals Corporation Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas
US7517880B2 (en) 1997-12-22 2009-04-14 Bayer Pharmaceuticals Corporation Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas
US7528255B2 (en) 1999-01-13 2009-05-05 Bayer Pharmaceuticals Corporation Hydroxy, ω-carboxyaryl substituted diphenyl ureas and dirivatives thereof as raf kinase inhibitors
US7678811B2 (en) 2002-02-11 2010-03-16 Bayer Healthcare Llc Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors
US7838541B2 (en) 2002-02-11 2010-11-23 Bayer Healthcare, Llc Aryl ureas with angiogenesis inhibiting activity
US7897623B2 (en) 1999-01-13 2011-03-01 Bayer Healthcare Llc ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
US7928239B2 (en) 1999-01-13 2011-04-19 Bayer Healthcare Llc Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas
US20110136809A1 (en) * 2004-04-30 2011-06-09 Bayer Pharmaceuticals Corporation Substituted Pyrazolyl Urea Derivatives Useful In The Treatment Of Cancer
US8076488B2 (en) 2003-02-28 2011-12-13 Bayer Healthcare Llc Bicyclic urea derivatives useful in the treatment of cancer and other disorders
US8110587B2 (en) 2002-02-11 2012-02-07 Bayer Healthcare Llc Aryl ureas as kinase inhibitors
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US8637553B2 (en) 2003-07-23 2014-01-28 Bayer Healthcare Llc Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions

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JPS5615272A (en) * 1979-07-17 1981-02-14 Ishihara Sangyo Kaisha Ltd N-benzoyl-n'-phenylurea compound, its preparation, and insecticide containing the same
JPS5731664A (en) * 1980-07-30 1982-02-20 Ishihara Sangyo Kaisha Ltd N-benzoyl-n'-pyridyloxyphenylurea derivative
US4366155A (en) 1981-03-30 1982-12-28 Eli Lilly And Company 1-Benzoyl-3-(6-oxopyridazinyl)ureas, compositions, and insecticidal method
US4511571A (en) * 1981-10-20 1985-04-16 Ciba Geigy Corporation N-(2-Pyridyloxyphenyl)-N'-benzoyl ureas, pesticidal compositions containing same and pesticidal methods of use
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Cited By (51)

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US4223033A (en) * 1979-08-24 1980-09-16 Zoecon Corporation Substituted pyridine methyl esters of naphthyl acids
US4310530A (en) * 1979-09-07 1982-01-12 Ishihara Sangyo Kaisha Ltd. N-benzoyl N-pyridyloxy phenyl urea
US4344951A (en) * 1979-09-07 1982-08-17 Ishihara Sangyo Kaisha Ltd. N-Benzoyl N'-pyridyloxy phenyl urea
US4321388A (en) * 1979-09-11 1982-03-23 Ishihara Sangyo Kaisha Ltd. N-benzoyl N'-pyridyloxy phenyl urea
EP0040179A2 (en) * 1980-05-14 1981-11-18 Ciba-Geigy Ag Phenylbenzoyl urea
EP0040179A3 (en) * 1980-05-14 1982-01-20 Ciba-Geigy Ag Phenylbenzoyl urea
US4418066A (en) * 1980-05-14 1983-11-29 Ciba-Geigy Corporation Phenylbenzoylureas
FR2492822A1 (en) * 1980-10-24 1982-04-30 Nissan Chemical Ind Ltd HETEROCYCLIC UREA COMPOUNDS CONTAINING ETHER OR THIOETHER BINDING, PROCESS FOR THEIR PREPARATION AND INSECTICIDE COMPOSITION CONTAINING SAME
US4425343A (en) 1980-10-24 1984-01-10 Nissan Chemical Industries, Ltd. Benzoazine ether or thioether linkage containing urea compounds, process for producing same and insecticides containing said compounds
US4577028A (en) * 1981-10-20 1986-03-18 Ciba-Geigy Corporation 5-Haloalkyl-pyridines
US4677127A (en) * 1981-11-10 1987-06-30 Ciba-Geigy Corporation Certain N-3-(3-chloro-5-trifluoromethyl-pyridyl-2-oxy)-4-phenyl-N'-2,6-difluorobenzoyl ureas, pesticidal compositions and methods of use
US4897486A (en) * 1981-11-10 1990-01-30 Ciba-Geigy Corporation 5-trifluoromethylpyridyl-2-oxy-4-fluoroanilines as intermediates
US4431667A (en) * 1981-12-04 1984-02-14 The Upjohn Company Imino ethers useful for controlling insect and arachnoid pests
US4602109A (en) * 1982-12-30 1986-07-22 Union Carbide Corporation Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation
US4659724A (en) * 1982-12-30 1987-04-21 Union Carbide Corporation Certain 1-[4-(5-cyano-2-pyridyloxy)phenyl-benzoyl ureas having pesticidal properties
US4540578A (en) * 1982-12-30 1985-09-10 Union Carbide Corporation Pesticidal phenoxypyridyl benzoyl ureas
US4973589A (en) * 1986-08-06 1990-11-27 Ciba-Geigy Corporation Method of preventing the reinfestation of dogs and cats by fleas
US4861799A (en) * 1986-10-03 1989-08-29 Ishihara Sangyo Kaisha Ltd. Benzoylurea compounds and pesticides containing them
US4985449A (en) * 1986-10-03 1991-01-15 Ishihara Sangyo Kaisha Ltd. N-benzoyl-N-pyridyloxy phenyl urea compounds and pesticide compositions containing them
US5036072A (en) * 1989-01-24 1991-07-30 Ishihara Sangyo Kaisha Ltd. Antiviral agent
US5098907A (en) * 1989-01-24 1992-03-24 Ishihara Sangyo Kaisha Ltd. Powdery pharmaceutical composition containing benzoyl urea, a dispersant and silicic acid
US5728719A (en) * 1991-12-23 1998-03-17 Virbac, Inc. Systemic control of parasites
US6344476B1 (en) 1997-05-23 2002-02-05 Bayer Corporation Inhibition of p38 kinase activity by aryl ureas
US20100160371A1 (en) * 1997-05-23 2010-06-24 Gerald Ranges Inhibition of p38 kinase activity by aryl ureas
US7517880B2 (en) 1997-12-22 2009-04-14 Bayer Pharmaceuticals Corporation Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas
US7625915B2 (en) 1997-12-22 2009-12-01 Bayer Healthcare Llc Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas
US20080009527A1 (en) * 1997-12-22 2008-01-10 Jacques Dumas Inhibition of raf kinase using aryl and heteroaryl substituted heterocyclic ureas
US7329670B1 (en) 1997-12-22 2008-02-12 Bayer Pharmaceuticals Corporation Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas
US7897623B2 (en) 1999-01-13 2011-03-01 Bayer Healthcare Llc ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
US7928239B2 (en) 1999-01-13 2011-04-19 Bayer Healthcare Llc Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas
US7351834B1 (en) 1999-01-13 2008-04-01 Bayer Pharmaceuticals Corporation ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7528255B2 (en) 1999-01-13 2009-05-05 Bayer Pharmaceuticals Corporation Hydroxy, ω-carboxyaryl substituted diphenyl ureas and dirivatives thereof as raf kinase inhibitors
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
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US7371763B2 (en) 2001-04-20 2008-05-13 Bayer Pharmaceuticals Corporation Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas
US20100152251A1 (en) * 2002-02-11 2010-06-17 Jacques Dumas Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors
US20040023961A1 (en) * 2002-02-11 2004-02-05 Bayer Corporation Aryl ureas with raf kinase and angiogenisis inhibiting activity
US7838541B2 (en) 2002-02-11 2010-11-23 Bayer Healthcare, Llc Aryl ureas with angiogenesis inhibiting activity
US8071616B2 (en) 2002-02-11 2011-12-06 Bayer Healthcare Llc Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors
US8110587B2 (en) 2002-02-11 2012-02-07 Bayer Healthcare Llc Aryl ureas as kinase inhibitors
US7678811B2 (en) 2002-02-11 2010-03-16 Bayer Healthcare Llc Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors
US9181188B2 (en) 2002-02-11 2015-11-10 Bayer Healthcare Llc Aryl ureas as kinase inhibitors
US8242147B2 (en) 2002-02-11 2012-08-14 Bayer Healthcare Llc Aryl ureas with angiogenisis inhibiting activity
US8618141B2 (en) 2002-02-11 2013-12-31 Bayer Healthcare Llc Aryl ureas with angiogenesis inhibiting activity
US8076488B2 (en) 2003-02-28 2011-12-13 Bayer Healthcare Llc Bicyclic urea derivatives useful in the treatment of cancer and other disorders
US20070020704A1 (en) * 2003-05-20 2007-01-25 Scott Wilhelm Diaryl ureas with kinase inhibiting activity
US8796250B2 (en) 2003-05-20 2014-08-05 Bayer Healthcare Llc Diaryl ureas for diseases mediated by PDGFR
US8637553B2 (en) 2003-07-23 2014-01-28 Bayer Healthcare Llc Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions
US20110136809A1 (en) * 2004-04-30 2011-06-09 Bayer Pharmaceuticals Corporation Substituted Pyrazolyl Urea Derivatives Useful In The Treatment Of Cancer
US8207166B2 (en) 2004-04-30 2012-06-26 Bayer Healthcare Llc Substituted pyrazolyl urea derivatives useful in the treatment of cancer

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